"Never try to take a fortified hill, especially if the Army on top is bigger than you are"
About this Quote
A businessman’s “military” advice like this is really a scalpel aimed at boardrooms, not battlefields. “Never try to take a fortified hill” reads like battlefield common sense, but the punchline is the second clause: “especially if the Army on top is bigger than you are.” It’s the deadpan demystification of hero narratives - the kind that make reckless competition sound noble. Hewlett isn’t praising courage; he’s warning against mistaking bravado for strategy.
The quote works because it translates competition into terrain. A fortified hill isn’t just an opponent; it’s an opponent with structural advantages: entrenched customer loyalty, distribution, patents, regulation, capital, culture. In corporate terms, the “hill” is where incumbents turn your attack into their home-field advantage. The subtext is almost managerial: don’t confuse motion with progress, and don’t let ego force you into the most expensive possible fight.
Context matters: Hewlett co-founded Hewlett-Packard and operated in an era when American business mythology loved the frontal assault - the disruptor before “disruption” became a buzzword. His line quietly argues for asymmetric thinking: go around the hill, change the map, or pick a different hill entirely. That “especially” is the tell. He’s not saying never compete; he’s saying never compete on the terms that make your loss predictable.
Underneath the pragmatism is a cultural critique: we romanticize uphill battles, but in real institutions, uphill usually means someone stacked the rules there on purpose.
The quote works because it translates competition into terrain. A fortified hill isn’t just an opponent; it’s an opponent with structural advantages: entrenched customer loyalty, distribution, patents, regulation, capital, culture. In corporate terms, the “hill” is where incumbents turn your attack into their home-field advantage. The subtext is almost managerial: don’t confuse motion with progress, and don’t let ego force you into the most expensive possible fight.
Context matters: Hewlett co-founded Hewlett-Packard and operated in an era when American business mythology loved the frontal assault - the disruptor before “disruption” became a buzzword. His line quietly argues for asymmetric thinking: go around the hill, change the map, or pick a different hill entirely. That “especially” is the tell. He’s not saying never compete; he’s saying never compete on the terms that make your loss predictable.
Underneath the pragmatism is a cultural critique: we romanticize uphill battles, but in real institutions, uphill usually means someone stacked the rules there on purpose.
Quote Details
| Topic | Witty One-Liners |
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